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Michael Jackson had the highest number of top hits at the Billboard Hot 100 chart during the 1980s (9 songs) in addition, Jackson remained the longest at the top of the Billboard Hot 100 chart during the 1980s (27 weeks).

Rock With You (1980)
Billie Jean (1983)
Beat It (1983)
Say Say Say (1983)
I Just Can’t Stop Loving You (1987)
Bad (1987)
The Way You Make Me Feel (1988)
Man In The Mirror (1988)
Dirty Diana (1988)

#2 George Michael – 8 Number Ones

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George Michael was one of the most successful artists of the Billboard Hot 100 during the 1980s, with four number-one singles as a solo artist, three with Wham! and one as a duet with Aretha Franklin.

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George Michael is the only artist to have two #1 year end songs of the 1980s.

Wake Me Up Before You Go-Go (1984)Careless Whisper (1985) #1 song of 1985
Everything She Wants (1985)
I Knew You Were Waiting For Me (1987)Faith (1987-1988) #1 song of 1987
Father Figure (1988)
One More Try (1988)
Monkey (1988)

#3
Madonna – 7 Number Ones

Like a Virgin (1984-1985)
Crazy For You (1985)
Live to Tell (1986)
Papa Don’t Be Preach (1986)
Open Your Heart (1987)
Who’s That Girl (1987)
Like a Prayer (1989)

Whitney Houston – 7 Number Ones

Saving All My Love You (1985)
How Will I Know (1986)
Greatest Love of All (1986)
I Wanna Dance with Somebody (Who Loves Me) (1987)
Didn’t We Almost Have It All (1987)
So Emotional (1988)
Where Do Broken Hearts Go (1988)

Phil Collins – 7 Number Ones

Against All Odds (Take a Look at Me Now) (1984)
One More Night (1985)
Sussuido (1985)
Separate Lives (1985)
A Groovy Kind of Love (1988)
Two Hearts (1989)
Another Day In Paradise (1989-90)